Regio- and Stereoselective Hydroamination of Alkynes Using an Ammonia Surrogate: Synthesis of N-Silylenamines as Reactive Synthons

被引：32

作者：

Lui, Erica K. J. ^{[1
]}

Brandt, Jason W. ^{[1
]}

Schafer, Laurel L. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

RING-TRANSFORMATION EQUILIBRIUM; SPONGE ALKALOID CERATAMINE; C-H ACTIVATION; INTERMOLECULAR HYDROAMINATION; IMIDO COMPLEXES; REVERSIBLE 1,2-RH-ELIMINATION; CATALYTIC HYDROAMINATION; N; N-BIS(SILYL); ENAMINES; HYDROCARBON ACTIVATION; EFFICIENT SYNTHESIS;

D O I：

10.1021/jacs.7b13783

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An anti-Markovnikov selective hydroamination of alkynes with N-silylamines to afford N-silylenamines is reported. The reaction is catalyzed by a bis(amidate)bis(amido)Ti(IV) catalyst and is compatible with a variety of terminal and internal alkynes. Stoichiometric mechanistic studies were also performed. This method easily affords interesting N-silylenamine synthons in good to excellent yields and the easily removable silyl protecting group enables the catalytic synthesis of primary amines.

引用

页码：4973 / 4976

页数：4

共 66 条

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